The Pineapple Primary: An Election Violence Threat That Required 500 Federal Marshals

By Karen Harris

Three-quarter length portrait of Mr. and Mrs. Frank J. Loesch voting at a voting poll center in a room in Chicago, Illinois, 1928. Mr. Loesch, founder of the Chicago Crime Commission, is standing with crutches, handing a ballot to a man standing behind a

Chicago has a long history of corrupt politics and organized crime, and tensions between two groups vying for control of the city (and a slice of its bootlegging profits) came to a head during the April 1928 Republican primary election, A.K.A. the "Pineapple Primary." It was full of voter intimidation, bombs, hired thugs, corrupt cops, and a heavy dose of Al Capone.

Big Bill v. Charles Deneen

Between 1915 and 1923, Chicago had been led by the Republican Mayor William "Big Bill" Thompson. During his tenure, he was embroiled in scandal after scandal, and despite his powerful political allies, he was forced to sit out the 1923 election. The race was won by Democrat William Dever, who wanted to reform the city with strict enforcement of Prohibition lawsAs such, neither freedom-loving Republicans nor the city's organized crime bosses were big Dever fans, so they teamed up like an alcoholic Justice League to get Big Bill back in office.

Once he was back on his throne, Thompson set his sights on seizing control of the Illinois Republican Party, but first, he had to get through his longtime rival, Senator Charles Deneen. The pair had a contentious relationship dating all the way back to 1904, when they clashed at the state convention. By 1928, they had split the Illinois Republican Party into two factions, each of which ran their own candidates for the offices up for grabs in that year's primary election.

Chicago Mayor William Hale Thompson. (Harris & Ewing/Wikimedia Commons)

The Pineapple Primary

One of the key races of the 1928 primary was the office of state attorney of Cook County. Naturally, Thompson wanted to elect one of his cronies to protect himself and his buddies from corruption charges, while Deneen wanted the opposite. As the race drew closer, mud was slung further and further until it exploded into violence—literally.

Late in the evening of March 26, a grenade exploded on the front porch of Deneen's home, and another was tossed into the home of his favored candidate for state attorney, John Swanson. Neither man was injured, but the blasts caused considerable damage. Deneen's team accused Thompson of organizing the bombings, and Thompson countered that Deneen and Swanson had probably bombed their own homes to set him up. From then on, the race became known as the "Pineapple Primary" because grenades were commonly called "pineapples" in the slang of the day.

Interestingly, a few days prior to the Deneen/Swanson bombings, a Republican ward committeeman with strong ties to organized crime, Giuseppe "Diamond Joe" Esposito, was shot to death on the street in front of his home. Esposito was a friend of Deneen with his own political aspirations who offered protection to bootleggers, rum runners, gamblers, and speakeasy operators and had run afoul of Al Capone. In fact, Esposito had received warnings that he was marked for death. Despite claims that his own bodyguards were behind the shooting, no one was arrested for Esposito's murder.

Pollwatchers kept voters safe. (

The End Of An Empire

As Election Day approached, it was feared that both Big Bill's and Deneen's men would prevent each other's followers from casting their votes by any means necessary, so the federal government sent 500 federal marshals into Chicago to keep the peace. The Illinois Supreme Court pulled an additional 3,000 people from the state's bar association, deputized them, and sent them into the city to serve as poll watchers.

Despite these measures, a candidate for the 20th ward committee, Octavius Granady, was run down and shot while in his car, a bailiff was shot and wounded during a separate attack, and much of the Windy City was too scared by these incidents and the whole grenade thing to turn out at all. Whatever the cause, those who did manage to cast their votes overwhelmingly supported Deneen's candidates in all three key races, marking the end of Big Bill Thompson's political empire.

After the Pineapple Primary, people were just plain sick of the violence and corruption surrounding Chicago-area elections. The head of the Chicago Crime Commission, Frank Loesch, paid a visit to Capone ahead of the general election, begging him to let the city vote without fear. Capone allegedly responded, "Alright, I'll have the cops send over squad cars the night before the election, jug all them hoodlums, and keep 'em in the cooler until the poll close." Capone kept his word, and the 1928 Chicago general election has gone down in history as the cleanest election in the city's history.

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Karen Harris


Karen left the world of academic, quitting her job as a college professor to write full-time. She spends her days with her firefighter husband and four daughters on a hobby farm with an assortment of animals, including a goat named Atticus, a turkey named Gravy, and a chicken named Chickaletta.